2-FLUOROADENINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4FN5
Molecular Weight	153.1172
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(F)=NC2=C1NC=N2

InChI

InChIKey=WKMPTBDYDNUJLF-UHFFFAOYSA-N

InChI=1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C5H4FN5
Molecular Weight	153.1172
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Characterization of an engineered human purine nucleoside phosphorylase fused to an anti-her2/neu single chain Fv for use in ADEPT.	2009-12-03	19958550
Structural basis for enzymatic evolution from a dedicated ADP-ribosyl cyclase to a multifunctional NAD hydrolase.	2009-10-02	19640846
Diastereocontrolled electrophilic fluorinations of 2-deoxyribonolactone: syntheses of all corresponding 2-deoxy-2-fluorolactones and 2'-deoxy-2'-fluoro-NAD+s.	2009-08-21	19958035
A limited sampling schedule to estimate individual pharmacokinetic parameters of fludarabine in hematopoietic cell transplant patients.	2009-08-15	19671874
Selective killing of tumors deficient in methylthioadenosine phosphorylase: a novel strategy.	2009-05-29	19478948
Structure of a mutant human purine nucleoside phosphorylase with the prodrug, 2-fluoro-2'-deoxyadenosine and the cytotoxic drug, 2-fluoroadenine.	2009-05	19388075
Key labeling technologies to tackle sizeable problems in RNA structural biology.	2008-06	19325801
Prodrug converting enzyme gene delivery by L. monocytogenes.	2008-04-10	18402662
Cloning and functional expression of a novel Gi protein-coupled receptor for adenine from mouse brain.	2008-02	17975009
Comparison of gene targeting efficiencies in two mosses suggests that it is a conserved feature of Bryophyte transformation.	2007-10	17565445
[(3)H]Adenine is a suitable radioligand for the labeling of G protein-coupled adenine receptors but shows high affinity to bacterial contaminations in buffer solutions.	2007-09	18404448
Nicotinamide 2-fluoroadenine dinucleotide unmasks the NAD+ glycohydrolase activity of Aplysia californica adenosine 5'-diphosphate ribosyl cyclase.	2007-04-03	17341094
Preparation of a fludarabine intermediate via selective alkylation of 2-fluoroadenine.	2006	16898412
Cytosine arabinoside affects multiple cellular factors and induces drug resistance in human lymphoid cells.	2005-08-01	15950950
Identification of a subversive substrate of Trichomonas vaginalis purine nucleoside phosphorylase and the crystal structure of the enzyme-substrate complex.	2005-06-10	15817485
Oligotide, a defibrotide derivative, protects human microvascular endothelial cells against fludarabine-induced activation, damage and allogenicity.	2005-05	15778728
Evidence for the functional expression and pharmacological characterization of adenine receptors in native cells and tissues.	2005-03	15604413
Synthesis and biological activity of 2-fluoro adenine and 6-methyl purine nucleoside analogs as prodrugs for suicide gene therapy of cancer.	2005	16248054
Preclinical evaluation of a prostate-targeted gene-directed enzyme prodrug therapy delivered by ovine atadenovirus.	2004-11	15343359
Enzymatic synthesis and 19F NMR studies of 2-fluoroadenine-substituted RNA.	2004-09-29	15382896
Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.	2004-02-26	14971900
Gene-directed enzyme prodrug therapy for prostate cancer in a mouse model that imitates the development of human disease.	2004-01	14716676
Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.	2003-11-17	14592485
Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-fluoroadenine.	2003-10	14609229
Synthesis of carbocyclic and acyclic nucleosides possessing 2-fluoroadenine derivatives and their inhibitory activities against Plasmodium falciparum SAH hydrolase.	2003	14510352
Fludarabine induces apoptosis, activation, and allogenicity in human endothelial and epithelial cells: protective effect of defibrotide.	2002-07-01	12070045
Gene therapy for prostate cancer delivered by ovine adenovirus and mediated by purine nucleoside phosphorylase and fludarabine in mouse models.	2002-06	12040457
Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells.	2001-02	11234887

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:55 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:55 GMT 2025`
Record UNII	2C8H3H4EBG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-FLUOROADENINE

Systematic Name

English

NSC-27364

Preferred Name

English

1H-PURIN-6-AMINE, 2-FLUORO-

Systematic Name

English

2-FLUORO-6-AMINOPURINE

Systematic Name

English

ADENINE, 2-FLUORO-

Systematic Name

English

FLUDARABINE PHOSPHATE IMPURITY, 2-FLUOROADENINE- [USP IMPURITY]

Common Name

English

2-FLUORO-1H-PURIN-6-AMINE

Systematic Name

English

2-FLUORO-7H-PURIN-6-AMINE

Systematic Name

English

FLUDARABINE PHOSPHATE IMPURITY D [EP IMPURITY]

Common Name

English

9H-PURIN-6-AMINE, 2-FLUORO

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45176